KR102153638B1 - Composition of Flavor In Oral Care Products - Google Patents

Abstract

The present invention is (N-ethoxycarbonylmethyl)-p-mentane-3-carboxamide (WS-5), N-(4-menthoxyphenyl)-p-mentanecarboxamide (prescholate SC1), N-ethyl-p-mentane-3-carboxamide (WS-3), N,2,3-trimethyl-2-isopropyl butanamide (WS-23), menthone glycerin acetal (prescholate MGA), menthyllac Oral comprising at least one cooling agent selected from the group consisting of tate (prescholate ML), monomentyl succinate and (1R, 3R, 4S)-3-methyl 3,6-dioxaheptanoate It relates to a flavor composition. The oral flavoring composition of the present invention not only improves freshness and sustains enhanced freshness, but also lowers irritation.

Description

Composition of Flavor In Oral Care Products}

The present invention relates to an oral flavoring composition capable of enhancing the refreshing, the most important emotional quality in oral care products.

Research on cooling agents has been actively conducted since the development of WS-3 (USP 4,178,459) by Wilkinson Sword in the 1970s, and is already being developed and marketed by a number of perfume companies, and commercial applications for this have been actively conducted. have.

Recently, studies are being conducted on a method of increasing the effect by mixing and applying refreshing enhancers, and P&G's Frescholate MGA + menthol and/or WS-3 and/or WS-23 are used in combination to enhance the refreshment or (Enhanced cooling properties, US 5,451,404 (1995)), a method of enhancing the refreshingness of chewing gum by using a mixture of WS-3, WS-23, ML, MGA, and menthyl succinate from Wigly is known. (Chewing gum: mixing at least two physiological cooling agents with a release modification material, WO 99/12734 to Wrigley.)

On the other hand, L-Menthol (l-menthol) is widely used as a fragrance that gives a cool feeling and a chilly and refreshing feeling, that is, a cooling effect to human skin, mouth, nose and throat. Has been. However, l-menthol lacks the persistence of the cooling effect, has a problem of irritation, and increases the amount of use thereof, the cooling effect is strengthened, but has a disadvantage of having a bad bitter taste.

Although it has been reported that a simple mixture between refreshment enhancers or a mixture of L-menthol and a refreshment enhancer, which has been used in the past, has been reported, further studies to solve the problem of the irritation of L-menthol while improving and sustaining the refreshment are insufficient reality.

U.S. Patent No. 5,451,404

Accordingly, the present inventors intend to provide an oral flavoring composition capable of lowering irritation to L-menthol while further improving the refreshing effect.

In order to achieve the above object, the present inventors have studied for an oral flavoring composition capable of reducing the irritation of L-menthol while improving the refreshment and sustaining the enhanced refreshing. As a result, it was confirmed the optimal composition that can promote and sustain the refreshing and completed the present invention.

The present invention is (N-ethoxycarbonylmethyl)-p-mentane-3-carboxamide (WS-5), N-(4-menthoxyphenyl)-p-mentanecarboxamide (prescholate SC1), N-ethyl-p-mentane-3-carboxamide (WS-3), N,2,3-trimethyl-2-isopropyl butanamide (WS-23), menthone glycerin acetal (prescholate MGA), menthyllac Oral comprising at least one cooling agent selected from the group consisting of tate (prescholate ML), monomentyl succinate and (1R, 3R, 4S)-3-methyl 3,6-dioxaheptanoate It provides a flavoring composition.

In the present invention, the oral flavoring composition refers to a composition including a fragrance material and a refreshing enhancer used to add a good fragrance and refreshment to oral care products including toothpaste, toothpaste, and the like. The oral flavoring composition may further include a solvent such as glycerin or propylene glycol for dissolving them in addition to the flavoring and refreshing enhancer.

In the present invention, the fragrance or fragrance material is a material used to add fragrance and refreshment to oral care products. The types of perfumes used in oral care products are well known and include, for example, L-menthol, peppermint, spearmint, anetol or eucalyptol. Among them, L-menthol is the substance that has the greatest influence on the freshness and irritation of oral care products.

In the present invention, the refreshing enhancer refers to a substance included in the oral flavor composition in order to improve the strength and duration of refreshing.

In one embodiment of the present invention, the oral flavoring composition may further comprise ethanol. By additionally including ethanol, there is an advantage in that the oral flavoring composition has a more excellent effect of improving the refreshment, the refreshing lasting longer, and lowering the irritation of L-menthol.

In one embodiment of the invention, the oral flavoring composition is N-ethyl-p-mentane-3-carboxamide (WS-3), N-(4-menthoxyphenyl)-p-mentanecarboxamide (press Cholate SC1) and ethanol. In the case of the oral flavoring composition of the above composition, the effect of improving refreshing, sustaining refreshing and reducing irritation is particularly excellent.

In one embodiment of the present invention, the oral flavoring composition is N-ethyl-p-mentane-3-carboxamide (WS-3), (N-ethoxycarbonylmethyl)-p-mentane-3-carboxa Mide (WS-5), N-(4-menthoxyphenyl)-p-mentanecarboxamide (prescholate SC1), and ethanol.

In another embodiment of the present invention, the oral flavoring composition is N-ethyl-p-mentane-3-carboxamide (WS-3), N-(4-menthoxyphenyl)-p-mentanecarboxamide ( Prescholate SC1), monomenthyl succinate and ethanol.

In another embodiment of the present invention, the oral flavoring composition is N-ethyl-p-menthan-3-carboxamide (WS-3), menthyl lactate (prescholate ML), N-(4-menthoxy Phenyl)-p-mentanecarboxamide (prescholate SC1) and ethanol.

When the oral flavoring composition has the above composition, it is particularly excellent in the effect of improving refreshment and reducing irritation.

In general, the oral flavoring composition is contained in an amount of 0.1 to 1% by weight of the total material used in the oral care product, and in one embodiment of the present invention, the refreshing enhancing agent is 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavoring composition. May be included as wealth. For example, the freshness enhancer may be included in an amount of 0.1 to 18 parts by weight, 0.1 to 16 parts by weight, 0.1 to 14 parts by weight, 0.1 to 12 parts by weight, or 0.1 to 10 parts by weight based on 100 parts by weight of the total oral flavor composition. When the refreshing enhancer is 0.1 to 20 parts by weight, the refreshing enhancing effect is more excellent. Conversely, when the refreshment enhancer is less than 0.1 parts by weight, the effect of improving the refreshment is weak, and when it exceeds 20 parts by weight, it is difficult to realize the feeling of use due to an increase in the price of the oral flavor composition and weakening of the overall flavor.

In one embodiment of the present invention, when ethanol is included in the oral flavoring composition, ethanol may be included in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavoring composition. For example, ethanol may be included in an amount of 0.1 to 18 parts by weight, 0.1 to 16 parts by weight, 0.1 to 14 parts by weight, 0.1 to 12 parts by weight, or 0.1 to 10 parts by weight, based on the total oral flavor composition. In the case of containing 0.1 to 20 parts by weight of ethanol, it is possible to further improve a refreshing effect, a refreshing sustaining effect, and an irritation reducing effect.

The present invention also provides an oral care article comprising the above oral flavoring composition. Oral care products refer to products used to maintain and/or enhance oral cleanliness or freshness, or to remove or relieve bad breath. The oral flavoring composition according to the present invention is suitable for oral use and can be used without limitation on the kind of oral care products. For example, the oral care product can be toothpaste, mouthwash, mouth spray, film-type mouthwash, tablet-type mouthwash or gum.

The toothpaste and toothpaste containing the oral flavor composition according to the present invention were prepared to evaluate the effect of improving refreshing, the lasting effect of refreshing, and the degree of irritation (Test Example 1). For the evaluation of the degree of refreshment and stimulation, a panel with excellent taste and smell functions was selected and the degree of refreshment felt over time from immediately after brushing was analyzed. As a result, it was confirmed that in the case of the oral flavoring composition according to the present invention, freshness was improved, the degree of persistence of the freshness was more excellent, and the intensity of irritation was low.

The oral flavoring composition of the present invention not only improves freshness and sustains enhanced freshness, but also lowers irritation.

Hereinafter, the present invention will be described in detail through examples. The following examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples. The present embodiments are provided to complete the disclosure of the present invention and to fully inform the scope of the invention to those of ordinary skill in the art to which the present invention belongs, and the present invention will be defined by the scope of the claims. Only.

[Production Example 1] Preparation of oral flavor composition

In the oral flavor composition of oral care products, the greatest factor in refreshing is L-Menthol, and the refreshing feeling varies depending on the content of L-menthol. Accordingly, the present invention minimizes experimental errors by preparing an oral flavor composition under the same conditions containing about 50% of L-menthol.

Specific experimental examples are shown in Tables 1 and 2 below.

(Based on 100g, %, w/w) Raw material name Experimental Example 1 Experimental Example 2 Experimental Example 3 Experimental Example 4 Experimental Example 5 Experimental Example 6 Experimental Example 7 Peppermint oil 20.0 20.0 20.0 20.0 20.0 20.0 20.0 Spearmint oil 5.0 5.0 5.0 5.0 5.0 5.0 5.0 L-menthol 50.0 50.0 50.0 50.0 50.0 50.0 50.0 Anetol 10.0 10.0 10.0 10.0 10.0 10.0 10.0 Eucalyptol 5.0 5.0 5.0 5.0 5.0 5.0 5.0 WS-3 10.0 4.5 6.0 7.0 WS-5 1.0 2.5 2.0 WS-23 3.0 Press Collate MGA Prescholate ML 1.0 Press Collate SC-1 0.5 1.0 Monomentyl succinate 5.0 1.0 (1R, 3R, 4S)-3-mentyl 3,6-dioxaheptanoate 6.0 ethanol 4.0 2.5 2.0 1.0 Propylene glycol 10.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0 100.0

(Based on 100g, %, w/w) Raw material name Experimental Example 8 Experimental Example 9 Experimental Example 10 Experimental Example 11 Experimental Example 12 Experimental Example 13 Peppermint oil 20.0 20.0 20.0 20.0 20.0 20.0 Spearmint oil 5.0 5.0 5.0 5.0 5.0 5.0 l-menthol 50.0 50.0 50.0 50.0 50.0 50.0 Anetol 10.0 10.0 10.0 10.0 10.0 10.0 Eucalyptol 5.0 5.0 5.0 5.0 5.0 5.0 WS-3 6.0 5.0 WS-5 2.0 6.0 1.5 WS-23 2.5 6.0 Press Collate MGA 6.0 2.0 Prescholate ML 7.0 2.0 3.0 Press Collate SC-1 0.5 Monomentyl succinate 3.0 (1R, 3R, 4S)-3-mentyl 3,6-dioxaheptanoate 4.0 ethanol 1.5 Propylene glycol 2.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0

A toothpaste was prepared according to the following method using the oral flavor composition having the composition according to Table 1 and Table 2.

① Measure each component according to the above content, mix and stir until completely dissolved.

② To prepare a toothpaste product by adding 1% by weight of the oral flavor composition of the above experiment to the toothpaste base.

[Test Example 1] Evaluation of refreshment and irritation

Test example 1-1. Refreshing evaluation

In order to evaluate the degree of improvement of the refreshment devised in the present invention, a panel composed of 30 people with excellent taste and olfactory functions was constructed, and a flavored toothpaste product and toothpaste for the oral flavor composition of the experimental example of Table 1 were prepared and initially brushed. The intensity of refreshing was evaluated on a 15-point scale.

The odor rate of the toothpaste product was 1.0% by weight, and the odor rate of the toothpaste was 0.2% by weight to prepare a test product.

1) Panel training

For the evaluation of the present invention, 12 panelists with excellent taste and olfactory functions were selected to evaluate the intensity of refreshing. Prior to evaluating the oral care products to which the oral flavoring composition according to the present invention was applied, repeated evaluation was performed to reduce errors between panels and to improve the efficiency of evaluation.

As an evaluation method, a 15-point rating was performed. The panel was trained by presenting a standard sample in units of 3 points, and evaluation was conducted six times, and the final correction was completed through a double blinded test. .

The composition of the standard sample is shown in Table 3, and the final correction results are shown in Table 4.

Standard sample (based on 100g, %, w/w) Raw material name Standard 1 Standard 2 Standard 3 Standard 4 Standard 5 Peppermint oil 20.0 20.0 20.0 20.0 20.0 Spearmint oil 5.0 5.0 5.0 5.0 5.0 l-menthol 40.0 45.0 50.0 55.0 60.0 Anetol 10.0 10.0 10.0 10.0 10.0 Eucalyptol 5.0 5.0 5.0 5.0 5.0 Propylene glycol 20.0 15.0 10.0 5.0 0.0 Sum 100.0 100.0 100.0 100.0 100.0

Panel training results Raw material name Full L-menthol
(%,w/w) Standard score Final Panel Score Standard deviation (σ) Acceptable error range Standard 1 50 3.0 2.89 0.34 3.0±0.34 Standard 2 55 6.0 6.11 0.27 6.0±0.27 Standard 3 60 9.0 8.89 0.30 9.0±0.30 Standard 4 65 12.0 12.10 0.19 12.0±0.19 Standard 5 70 15.0 14.85 0.26 15.0±0.26

2) Refreshing evaluation method

2-1) Toothpaste evaluation

① Squeeze 1.5g of toothpaste into the same toothbrush.

② Brush your teeth using the method used by the panels and brush your teeth for about 90 seconds.

③ Gargle twice at the host's request.

④ Brush your teeth again for 1 minute.

⑤ Perform the final gargle to complete brushing within 20 seconds.

⑥ Evaluate the intensity of freshness immediately after brushing.

⑦ Measure the intensity of refreshing at 2, 5, 10, 20, and 30 minutes immediately after brushing to evaluate the persistence of refreshing.

2-2) Evaluation of toothbrushing solution

① Subdivide 15ml of toothpaste into the prepared reagent cup.

② Put the subdivided toothpaste in your mouth and gargle for 20 seconds.

③ Spit out the toothpaste and gargle again with 20ml of purified water for 5 seconds, and then evaluate the intensity of refreshing.

④ Like toothpaste, evaluate the persistence of refreshing at 2, 5, 10, 20, and 30 minutes.

3) Refreshing evaluation result

A) Degree of improvement of refreshment

As a result of evaluating the toothpaste and toothpaste composition prepared using Experimental Example 1-13, it was found that the refreshing effect of Experimental Examples 2 to 13 using the refreshing enhancer was excellent. (p<0.05)

In addition, in Experimental Examples 5, 7, 11, 12 and 13, it was found that the degree of improvement of the refreshment was particularly excellent.

It was found that toothpaste and toothpaste showed similar trends.

Evaluation result of the degree of refreshment improvement Experimental group toothpaste Gargling Experimental Example 1 9.45±0.27 9.75±0.29 Experimental Example 2 9.87±0.25 9.98±0.26 Experimental Example 3 11.51±0.31 11.25±0.21 Experimental Example 4 10.08±0.22 10.24±0.24 Experimental Example 5 13.78±0.28 12.48±0.23 Experimental Example 6 10.24±0.30 10.13±0.31 Experimental Example 7 12.96±0.29 12.08±0.33 Experimental Example 8 10.05±0.33 10.13±0.27 Experimental Example 9 10.15±0.25 10.01±0.23 Experimental Example 10 10.11±0.24 10.19±0.22 Experimental Example 11 11.89±0.29 11.67±0.25 Experimental Example 12 12.02±0.31 11.87±0.39 Experimental Example 13 13.41±0.31 12.83±0.25

B) Refreshing lasting intensity

The sustained strength of refreshing was found to be significantly superior to Experimental Example 1 in Experimental Examples 2 to 13 using the refreshing enhancer.

In addition, it was found that the sustained strength of refreshing was particularly excellent in Experimental Examples 5, 7 and 13.

Experimental Example 6 and Experimental Example 9 evaluated the sustained intensity of refreshing with or without ethanol, and the intensity of initial refreshing was similar, but it was determined that the persistence of refreshing over time was better in Experimental Example 6 including ethanol. (p<0.05)

In particular, it was investigated that when the time elapsed for more than 30 minutes, when the refreshment enhancer of the present invention and ethanol were used in combination compared to Experimental Example 1, about 7 times or more strong refreshing was maintained.

Refreshing lasting strength evaluation result (toothpaste) toothpaste Early 2 minutes 5 minutes 10 minutes 20 minutes 30 minutes Experimental Example 1 9.45 5.51 3.42 2.01 1.09 0.41 Experimental Example 2 9.87 9.88 7.45 6.41 5.55 3.25 Experimental Example 3 11.51 11.02 9.13 7.68 6.01 4.01 Experimental Example 4 10.08 10.56 8.74 6.25 4.77 3.91 Experimental Example 5 13.78 14.03 12.91 12.03 8.52 6.33 Experimental Example 6 10.24 10.36 8.44 6.25 4.57 3.89 Experimental Example 7 12.96 13.23 10.47 7.99 6.41 5.03 Experimental Example 8 10.05 10.23 8.51 6.23 4.44 3.52 Experimental Example 9 10.15 10.24 8.01 5.89 4.08 3.32 Experimental Example 10 10.11 10.56 8.57 6.74 4.86 3.21 Experimental Example 11 11.89 12.1 9.89 7.69 6.12 4.34 Experimental Example 12 12.02 12.48 10.01 7.12 5.92 4.22 Experimental Example 13 13.41 13.89 12.43 10.56 8.84 5.29

Refreshing lasting strength evaluation result (molar solution) Gargling Early 2 minutes 5 minutes 10 minutes 20 minutes 30 minutes Experimental Example 1 9.75 7.01 5.15 1.12 0.85 0.21 Experimental Example 2 9.98 8.59 6.03 4.01 2.99 2.07 Experimental Example 3 11.25 9.99 7.15 4.56 3.12 2.74 Experimental Example 4 10.24 8.74 5.87 3.99 2.15 2.11 Experimental Example 5 12.48 11.05 8.9 7.01 4.98 3.56 Experimental Example 6 10.13 8.34 6.15 4.74 2.91 1.88 Experimental Example 7 12.08 10.87 8.09 6.45 4.12 3.15 Experimental Example 8 10.13 8.71 5.89 4.78 2.91 2.09 Experimental Example 9 10.01 8.41 5.69 4.01 2.59 1.45 Experimental Example 10 10.19 8.74 7.12 5.78 3.26 1.99 Experimental Example 11 11.67 10.77 6.99 5.45 3.78 2.41 Experimental Example 12 11.87 10.45 7.65 6.02 4.07 2.89 Experimental Example 13 12.83 12.11 9.15 7.27 5.33 4.14

Test example 1-2. Irritation evaluation

1) How to evaluate irritation

The intensity of irritation was evaluated in toothpaste with relatively high irritation depending on use. The evaluation method is as follows.

① Squeeze 1.5g of toothpaste into the same toothbrush.

② Brush your teeth using the method used by the panels and brush your teeth for about 90 seconds.

③ Gargle twice at the host's request.

④ Brush your teeth again for 1 minute.

⑤ Perform the final gargle to complete brushing within 20 seconds.

⑥ Evaluate the intensity of irritation immediately after brushing and 5 minutes after brushing.

The evaluation is on a 5-point scale, and if there is little stimulation, it is evaluated as 1 point, and if the stimulation is very severe, it is evaluated as 5 points.

2) stimulus evaluation result

Table 8 shows the results of evaluation of the intensity of the feeling of stimulation. As a result, in Experimental Examples 3, 5, 6, 7 and 13, the feeling of irritation was generally evaluated to be low.

Through the results of Experimental Example 6 and Experimental Example 9 showing the intensity of the sensation with or without ethanol, it was found that the degree of sensation was low initially and after 5 minutes in Experimental Example 6 including ethanol (p<0.05). This, in particular, suggests that the experimental example containing ethanol can exhibit a better feeling of use due to the low intensity of the stimulation feeling.

Results of evaluation of the intensity of irritation Experimental toothpaste group Immediately after brushing 5 minutes later Experimental Example 1 3.46±0.73 2.88±0.62 Experimental Example 2 3.15±0.67 2.77±0.24 Experimental Example 3 2.98±0.59 2.48±0.44 Experimental Example 4 3.22±0.58 2.86±0.48 Experimental Example 5 2.96±0.62 2.42±0.59 Experimental Example 6 2.97±0.58 2.40±0.48 Experimental Example 7 2.91±0.53 2.48±0.41 Experimental Example 8 3.18±0.72 2.83±0.66 Experimental Example 9 3.41±0.65 2.84±0.63 Experimental Example 10 3.19±0.73 2.66±0.60 Experimental Example 11 3.03±0.97 2.72±0.69 Experimental Example 12 3.12±0.85 2.73±0.69 Experimental Example 13 2.86±0.71 2.44±0.49

Claims (10)

Oral flavoring composition comprising N-(4-menthoxyphenyl)-p-mentanecarboxamide, N-ethyl-p-mentane-3-carboxamide and ethanol as a cooling agent.
The method of claim 1,
The oral flavoring composition is an oral flavoring agent further comprising at least one selected from the group consisting of (N-ethoxycarbonylmethyl)-p-mentane-3-carboxamide, monomentyl succinate, and menthyl lactate Composition.
The oral flavoring composition of claim 1, wherein the freshness enhancing agent is contained in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavoring composition.
The oral flavoring composition of claim 1, wherein ethanol is contained in an amount of 0.1 to 20 parts by weight based on 100 parts by weight of the total oral flavoring composition.
An oral care article comprising the oral flavoring composition of any one of claims 1 to 4.
The oral care product of claim 5, wherein the oral care product is toothpaste, mouthwash, mouth spray, film-type mouthwash, tablet-type mouthwash or gum.
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